#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/57/1515719.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1515719
loop_
_publ_author_name
'Mondal, Barnali'
'Captain, Burjor'
'Ramamurthy, V.'
_publ_section_title
;
 Photodimerization of HCl salts of azastilbenes in the solid state.
;
_journal_issue                   6
_journal_name_full
'Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_page_first              891
_journal_page_last               894
_journal_paper_doi               10.1039/c1pp05070b
_journal_volume                  10
_journal_year                    2011
_chemical_formula_sum            'C13 H7 Cl F5 N'
_chemical_formula_weight         307.65
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                66.6060(8)
_cell_angle_beta                 71.9947(9)
_cell_angle_gamma                84.0524(9)
_cell_formula_units_Z            2
_cell_length_a                   8.3749(5)
_cell_length_b                   8.3985(5)
_cell_length_c                   10.2024(7)
_cell_measurement_reflns_used    3947
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.28
_cell_volume                     626.21(7)
_computing_cell_refinement       'SAINT+ V7.46A (Bruker, 2007)'
_computing_data_collection       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_data_reduction        'SAINT+ V7.46A (Bruker, 2007)'
_computing_molecular_graphics    'XSHELL v4.02 (Bruker, 2000)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7234
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  0.9722
_exptl_absorpt_correction_T_min  0.8263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS 2007/4 Bruker)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0746P)²+0.3027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1532
_refine_ls_wR_factor_ref         0.1575
_reflns_number_gt                2145
_reflns_number_total             2459
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1pp05070b.txt
_cod_data_source_block           13-PentaFluoroStilbazole-HCl-Salt
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1515719
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.17073(8) 0.66726(9) 0.48161(8) 0.0712(3) Uani 1 1 d .
F1 F 0.5336(3) 0.6349(4) 0.1501(3) 0.1138(7) Uani 1 1 d .
F2 F 0.3268(4) 0.8927(3) 0.0730(3) 0.1385(10) Uani 1 1 d .
F3 F 0.0191(3) 0.8282(3) 0.0682(3) 0.1357(11) Uani 1 1 d .
F4 F -0.0784(3) 0.4999(4) 0.1416(3) 0.1178(8) Uani 1 1 d .
F5 F 0.1296(3) 0.2397(3) 0.2167(3) 0.1106(7) Uani 1 1 d .
N1 N 0.8200(4) -0.2302(5) 0.4070(3) 0.0941(10) Uani 1 1 d .
H1A H 0.8877 -0.3120 0.4352 0.113 Uiso 1 1 calc R
C1 C 0.8536(4) -0.0742(7) 0.3876(4) 0.0944(11) Uani 1 1 d .
H1 H 0.9506 -0.0531 0.4048 0.113 Uiso 1 1 calc R
C2 C 0.7540(4) 0.0557(4) 0.3441(4) 0.0833(9) Uani 1 1 d .
H2 H 0.7812 0.1662 0.3321 0.100 Uiso 1 1 calc R
C3 C 0.6103(3) 0.0294(4) 0.3160(3) 0.0649(7) Uani 1 1 d .
C4 C 0.5770(4) -0.1376(5) 0.3385(4) 0.0805(9) Uani 1 1 d .
H4 H 0.4811 -0.1634 0.3224 0.097 Uiso 1 1 calc R
C5 C 0.6852(6) -0.2655(4) 0.3844(4) 0.0950(11) Uani 1 1 d .
H5 H 0.6628 -0.3788 0.3998 0.114 Uiso 1 1 calc R
C6 C 0.4700(6) 0.1413(6) 0.2681(5) 0.0678(9) Uani 0.70 1 d P
H6 H 0.3800 0.0905 0.2625 0.081 Uiso 0.70 1 calc PR
C7 C 0.4721(7) 0.3048(6) 0.2350(4) 0.0646(10) Uani 0.70 1 d P
H7 H 0.5644 0.3520 0.2405 0.077 Uiso 0.70 1 calc PR
C8 C 0.3385(3) 0.4258(4) 0.1882(3) 0.0646(7) Uani 1 1 d .
C9 C 0.3824(4) 0.5958(4) 0.1501(3) 0.0725(7) Uani 1 1 d .
C10 C 0.2777(5) 0.7311(4) 0.1094(3) 0.0845(9) Uani 1 1 d .
C11 C 0.1232(5) 0.6989(5) 0.1067(3) 0.0824(9) Uani 1 1 d .
C12 C 0.0737(4) 0.5332(5) 0.1435(3) 0.0780(8) Uani 1 1 d .
C13 C 0.1806(4) 0.4014(4) 0.1818(3) 0.0718(7) Uani 1 1 d .
C6B C 0.5563(8) 0.2151(10) 0.2707(8) 0.0409(13) Uani 0.30 1 d P
H6B H 0.6181 0.3023 0.2687 0.049 Uiso 0.30 1 calc PR
C7B C 0.4084(10) 0.2470(12) 0.2322(8) 0.0394(15) Uani 0.30 1 d P
H7B H 0.3517 0.1565 0.2337 0.047 Uiso 0.30 1 calc PR
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C5 121.1(3)
N1 C1 C2 121.7(3)
C1 C2 C3 120.7(3)
C4 C3 C2 116.3(3)
C4 C3 C6B 147.5(4)
C2 C3 C6B 96.2(4)
C4 C3 C6 108.1(3)
C2 C3 C6 135.5(3)
C6B C3 C6 39.3(3)
C5 C4 C3 119.7(3)
N1 C5 C4 120.4(3)
C7 C6 C3 121.2(5)
C6 C7 C8 125.2(6)
C9 C8 C13 115.2(3)
C9 C8 C7 111.4(3)
C13 C8 C7 133.4(3)
C9 C8 C7B 141.0(4)
C13 C8 C7B 103.8(4)
C7 C8 C7B 29.9(3)
F1 C9 C10 117.0(3)
F1 C9 C8 120.3(3)
C10 C9 C8 122.7(3)
F2 C10 C11 120.3(3)
F2 C10 C9 120.3(4)
C11 C10 C9 119.5(3)
F3 C11 C10 120.5(4)
F3 C11 C12 119.4(4)
C10 C11 C12 120.1(3)
F4 C12 C13 120.1(3)
F4 C12 C11 120.6(3)
C13 C12 C11 119.3(3)
F5 C13 C12 118.3(3)
F5 C13 C8 118.5(3)
C12 C13 C8 123.2(3)
C7B C6B C3 115.3(7)
C6B C7B C8 120.7(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C9 1.340(4)
F2 C10 1.330(4)
F3 C11 1.331(3)
F4 C12 1.339(4)
F5 C13 1.340(4)
N1 C1 1.292(5)
N1 C5 1.304(5)
C1 C2 1.319(5)
C2 C3 1.378(4)
C3 C4 1.372(4)
C3 C6B 1.504(8)
C3 C6 1.505(6)
C4 C5 1.362(5)
C6 C7 1.278(7)
C7 C8 1.492(6)
C8 C9 1.380(4)
C8 C13 1.384(4)
C8 C7B 1.499(9)
C9 C10 1.370(5)
C10 C11 1.360(5)
C11 C12 1.363(5)
C12 C13 1.359(4)
C6B C7B 1.381(10)
